


Personal Assistance

by DRHPaints



Category: American (US) Actor RPF, Bill Hader - Fandom, Bill Hader RPF, US Comedians RPF
Genre: Anxiety, Anxiety Disorder, Boss/Employee Relationship, Dirty Talk, Explicit Language, Explicit Sexual Content, F/M, One Shot, Pining, Quarantine, Smut, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-10-28
Updated: 2020-10-28
Packaged: 2021-03-08 21:01:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,232
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27243115
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Bill nurses a crush on his assistant, Kara. When she comes to his door bearing cookies after he finishes up with the Austin Film Festival, Bill asks if she wants to stick around to watch a movie and they discover their long-held attraction for one another.
Relationships: Bill Hader/Original Female Character
Comments: 2
Kudos: 12





	Personal Assistance

**Author's Note:**

> Written for soggybucket on tumblr. Hope you enjoy!

Bill knew it was a bad idea. He  _ knew _ it. It wasn’t often he let his dick do the thinking for him. Bill simply wasn’t that kind of guy. But when his former assistant got a job as a PA for a big time action movie and gave notice, Bill had no choice but to start conducting interviews, and it happened to coincide with a drought in his love life.

So when Kara came in, casual jeans and flannel doing nothing to hide her voluptuous curves, hair a mass of crimson waves gathered in a bun atop her head, one tantalizing strand dangling down her swan-like neck as she smiled eagerly and explained her goals, Bill was mesmerized.

It wasn’t as if Kara weren’t qualified. She was. Incredibly so. Somehow, and Bill hadn’t discerned her trick quite yet, Kara was able to anticipate many of his needs before he even expressed them. Empathetic to a fault, Kara could sense when Bill was stressed, and he would receive a text in the writer’s room, often while he was mid-sigh.  _ Just found a coupon for a massage. Want me to schedule you one? You have two hours free tomorrow. _

__ Or Kara could tell when Bill didn’t vibe with someone. A tension around his pink lips. A glint in his cobalt eyes, and Kara would slyly lean in after they left. “You want me to get you out of that? Make up an excuse?” As someone who hated confrontation, Bill found this particular skill invaluable.

So when Bill finished up with the Austin Film Festival panel, saying goodbye and closing Zoom, only to hear a knock at his door, it was no surprise to see Kara, removing her mask to reveal a warm smile and holding a bakery box aloft.  _ How did she know I had a sugar craving? _

__ “Hey Bill.” Kara came in once he stepped aside and Bill felt slightly self conscious in his Camp Funtime t-shirt and shorts. Then, realizing he was just on camera for anyone in the world to see, Bill told himself he was being ridiculous. “How’d the panel go?”

“Good.” Bobbing his head, Bill tried not to follow her with his eyes as Kara made her way to the kitchen. Tried not to notice the pleasant way her ass switched beneath her green sundress. “At least, I think so. The moderator was amazing. Very professional. Didn’t interrupt at all.”

“Oh that’s great.” Kara flipped open the bakery box, revealing fresh ginger snap cookies from his favorite place and extending it his way. “Nothing like that douchebag from  _ The Atlantic _ Doc Now panel, huh?”

Rolling his eyes, Bill sighed heavily. “Oh fuck, don’t remind me. And…” Bill stretched out his lower lip, shaking his head and holding up his palms. “I think I’d better stay away from those…” Patting his belly, he frowned. “I’m never going to lose this if you keep bringing me treats.”

“Aw, come on.” Kara leaned forward, giving him an admiring jiggle with a smile. “You look fantastic. And you love them. What’s the harm?”

A blotchy pink hue crept up Bill’s neck, eyes shifting as a crooked, goofy grin spread over his face. “Okay...maybe just one…” 

They sat at the kitchen table and, biting into a second, Kara raised an eyebrow. “Milk?”

“Yes, please.” Bill muttered around a mouthful of confection. 

Kara stood, giving Bill’s broad shoulder a squeeze before retrieving two glasses from the cupboard. Part of Bill wanted to tell her not to touch him. Wanted to say it wasn’t professional, that Kara should keep her distance. But if he was honest with himself, Bill would miss it keenly were she to stop. After months in quarantine, his skin was hungry for contact. And besides, Bill witnessed Kara around others. Men, women, whoever, it didn’t matter. Much like himself, she was a generally affectionate person. It didn’t mean anything.

Placing a glass at his elbow, Bill drank deep, nodding. “Thank you.”

“Welcome.” Kara smiled. “Fuck it, I’m having a third. I don’t care if I get chunky in quarantine. No one’s seeing my fat ass anyway.” Chomping down, Kara let out a delighted sigh far too close to a moan and it made Bill itchy all over.

Bill shook his head, giving in and grabbing a second cookie. “You’re not fat. You’re beautiful.” Realizing what he said, Bill looked down at the table, trying to focus on his chewing. Moment of silence stretching interminably, he wished Kara would say something to break the tension. Bill thought if he gave in to the nagging urge to start apologizing it would only serve to make things more awkward.

“You think so?” Glancing up, Bill saw Kara’s head tilted, green eyes curious.

Lifting a shoulder, Bill tried to keep his voice casual. “Sure. Yeah.” Nose flaring, he was grateful Kara couldn’t see his fingers nervously tapping his thick thigh beneath the table.

“Thanks, Bill.” She beamed at him and Bill couldn’t help but mirror her gleeful visage. Sitting back, Kara patted her stomach. “Ugh. I’m going to feel like trash now. I should really go running or something, but…” Shrugging, she finished the rest of her drink. “I’m sure I’ll just end up flopping down and streaming something instead. You want anymore?” Kara held out the box and Bill shook his head. Folding it, she placed it on his counter and snatched up her purse.

“Alright, well, I guess I’ll head out. See you Wednesday then?”

Bill wasn’t ready for her to go. After days alone in the house, limited to talking to people digitally, her presence was a balm Bill didn’t know he needed until she was standing in his doorway.

“Hey, um…” Folding his lip under, Bill shifted in his chair. “You want to hang out for a bit? Watch a movie or something?”

“Oh.” Corners of her mouth turning down in appraisal, Kara placed her hands on her thighs. “Yeah. Sure, why not?”

“Great.” More relieved than he was willing to admit, Bill followed her to the living room and opened his massive cabinet of Blu-rays. “Alright, so…” Chewing on his lip, Bill scanned the titles. “ _ The Big Lebowski?” _ He raised an eyebrow and Kara nodded enthusiastically. “Great. Honestly…” Bill popped it in, shaking his head. “I could probably watch this thing every week.”

“Me too. So brilliant.” Kara grinned and he joined her on the couch, conscious of not sitting too close as he hit play. 

No matter how many times he viewed it, Bill giggled endlessly at the Coen Brothers’ masterpiece. But when he selected the film, Bill didn’t think about Maude. Julianne Moore’s character, as she came swinging into the shot, naked, Bill squirmed, all too aware that he spent a significant amount of time lately picturing a naked, pale redhead, who, coincidentally, also enjoyed painting, and he tried not to allow his mind to wander as Kara lounged beside him.

“Ugh, she’s stunning, isn’t she?” Kara shook her head, tucking her legs up on the cushion. “I wish I looked like that.”

“Yeah, she is…” Hands crawling over themselves in his lap, Bill cleared his throat. “You...you are, too, though…” Resolutely maintaining his focus on the screen, Bill clenched his teeth, muscle in his sharp jaw popping. Kara was silent for a long time. Finally Bill risked a glance in her direction. She was picking at a loose string on the fabric of her skirt. “I...I’m sorry.” Bill muttered softly. “I shouldn’t have said that. I didn’t mean to make you uncomfortable or...or anything. I just…” Swallowing, Bill’s prominent dark eyebrows knit together. “I don’t know…”

“No, it’s, um…” Nodding, Kara bit her lip. “I liked it. It’s just…” Turning her face back towards the kitchen, Kara blinked, and when she spoke again her voice was barely above a whisper. “You’re so sexy, Bill…”

Turning so fast he heard his neck crack, Bill tilted his head. “R-really?”

Kara raised a shoulder. The thread she pulled was a good half a foot long now. “Yeah...I’m..I’m sorry. I know I shouldn’t…” Shaking her head, Kara frowned. “I know I shouldn’t be looking at you like that. You being my boss and all…” She shifted uncomfortably. “And I really like this job so...fuck.” Kara brought a hand to her brow. “That was really fucking stupid of me to say.”

“Is it okay, if, um…” Bill inched toward her slightly. “If I don’t think it was?”

Kara met his oceanic eyes.”You...you don’t?” Shaking his head, Bill’s heart thundered, drowning out the sound of the movie. Her hand tentatively reached out to cover his own and Bill flipped his palm, interlacing their fingers.

Kara’s face. Close. Her mouth. Lips touching his own, Bill allowed his eyes to close, the soft sigh of contentment bubbling up from his chest unintentional as her tongue crept past his teeth and her elegant fingers wound into his mussed chestnut waves.

“ _ Bill… _ ” Whispering, Kara parted from their kiss for a moment before her body folded into him. Warm. Supple. Bill’s hands stuttered over her arm. Unsure. Timid. 

Bill told himself to breathe, to relax.  _ She likes you. It’s fine. Just be here.  _ But unlike his performances, Bill couldn’t think of a small way to purposefully mess up and trick his brain into thinking:  _ Okay, you failed and the world didn’t end. You’re still here. You can do this. _

Hand grazing his firm chest, Kara noticed Bill was rigid beneath her touch, his lips seemingly struggling to keep up. “Bill?” Breaking away, she stroked his cheek, sporting a heavy stubble. “Everything okay?”

“Yeah, yeah…” Flashing a wide smile, Bill’s deep blue eyes were pools of anxiety, and when Kara gave his vast shoulder a squeeze, tilting her head, he sighed. “Sorry.” Holding up his palms, a giggle crept past Bill’s lips.  _ Why? Why can’t I ever control it. Even in the worst times.  _ “I’m just nervous.” Bill found that sometimes saying it out loud, speaking the words, would alleviate the tension in himself. Almost as if he were challenging the monster who perched on his shoulder, calling it out, not permitting it to hide in the darkness, but exposing it to the light, forcing it to scurry to the dank recesses until the next daunting situation approached.

“Me too.” Kara chuckled, patting his hand. “I just don’t show it as much, is all. But…” Shaking her head, Kara sat back and removed her fingers. “We don’t have to do anything. I don’t want to make you uncomfortable.”

For the first time, Kara’s interpretation of Bill’s desires was dead wrong. “No...no, I…” Bill was never quite good at saying these sorts of things aloud. “I want you.” Voice almost impossibly small, Bill stared at the cushion between them. 

Kara swiveled in, her nose trailing down his cheek, whiskers chafing her skin. “I want you, too, Bill.” She whispered.

Nodding, Bill turned into her, caught Kara’s mouth. Pink lips weaving against hers, Kara tossed a leg over his lap as Bill’s large hand went to her waist. Kara grinding into him, Bill discovered he was achingly hard after only a couple of minutes and chided himself for not jerking off that morning. But Kara didn’t seem to mind his quick response, bearing down onto Bill’s burgeoning erection through the thin fabric of her panties, moaning against his mouth and rolling her hips.

Swooping into his neck, Kara’s lips brushed over his skin, inhaling Bill’s intoxicating scent, rich, unctuous, as she buried her fingers in his dark locks, panties soaking as she sought friction. “Fuck, Bill, you’re making me so wet…”

Sizable hands gliding up her creamy thighs, Bill’s eyes darted around the room. He couldn’t think of anything to say, and Jeff Bridges on the screen in front of him wasn’t helping. Lassoing a powerful arm around Kara, Bill leaned them forward and flipped off the TV before settling back. 

“Kara, you’re so beautiful, I…” Clearing his throat, Bill cautiously inched his way up to her hips, breath hitching when he caught sight of her black panties. “I think about you all the time.”

“Yeah?” Kara nipped at his earlobe and Bill let his head fall back, let his pelvis rise, cock swiping tantalizingly between her legs. “What do you think about, Bill? Tell me.”

“I, um…” Eyes shut tight, Bill folded his lips under, starting to rock into Kara’s heat. “I think about touching you…” His voice came out even higher than usual, curling up at the end as though he were asking her a question, and Bill inwardly cringed.

“Mmm…” Humming, Kara rubbed her body against him, nuzzling. “Me too, Bill. I can’t stop. I just…” Emitting a breathy sigh, Kara’s hands roamed. “I think about touching your face…” Fingers flowing over his sculpted jaw, Bill leaned into her. “Your body…” She massaged her way over his firm chest and down Bill’s expansive shoulders. Pausing above the waistband of his shorts, Kara’s voice sank, deep, sultry. “ _ Your cock _ …”

Bill let out a shuddering exhale as Kara played with the tendrils at the base of his neck with her other hand. “You want me to touch you, Bill?”

Bill only trusted himself to nod, and when her delicate hand snuck beneath the waistband of his shorts, grasping his cock, Bill released something between a whimper and a squeak. “You, um…” Fingers tiptoeing between her thighs, Bill planted a scratchy kiss to the corner of her jaw. “You want me to?”

“Yeah…” Kara pumped him and Bill breached her panties, groaning low with satisfaction when he dipped into her slickness and twirled over her clit. Rutting into his hand, Kara claimed his mouth again, their tongues knitting together as their wrists worked between them.

Fiddling his fingers, Kara’s lips grew uncoordinated and she rested her forehead against his. “ _ Bill! Fuck, _ I’ve wanted you for so long…”

“Me too.” Bill thrust into the circle of her palm, couch creaking beneath them as Kara bounced on his hand.

“ _ Bill, I...I… _ ” Kara whined, her fingers digging into his wide back. “I think about fucking you all the time. I want your big cock inside me so badly.”

Kissing her open mouth, Bill hastened his ministrations, emboldened when Kara buried her face in the crook of his neck and the pitch of her ecstasy rose as her pelvis drove forward.

“Kara…” Strong arm at the small of her back, Bill held her to himself. “I want to be inside of you.” Racing over her clit, Kara’s thighs quaked around his escalating hips. “I...I wanna fuck you.” Bill tugged down her dress, tracing her collarbone with his lips. “So  _ deep _ . So…” Hold tightening over her as she seized over him, shrieking, Bill whispered into her neck. “So fucking much, Kara. I...I need to fuck you.  _ Please _ .”

Dripping over his fingers, Kara caught her breath and leaned back, nodding against Bill’s cheek. “Yeah, yeah.” Swallowing, she kissed the corner of his mouth. “Do you, um...do you have a condom?”

“Yeah. Hang on.” Bill gave her ass a gentle pat and Kara extricated herself. Jogging to his bedroom, Bill’s cock was devastatingly hard beneath his shorts as he rifled in his bedside drawer, praying the condoms weren’t expired. Bill found one, narrowing his eyes at the date and sighing with relief as he rushed back to the living room.

When he returned he held the tiny package aloft with a smile. Then Bill spotted Kara stepping out of her panties and swallowed, slowing in the last few feet to the couch. Sitting down, Bill had difficulty looking at her as Kara lowered himself on top of him, until she tipped his square chin up to meet her gaze. “You alright?”

Catching the expression of want, of solace, of lust, of comfort in her emerald eyes, Bill smiled. “Yeah. I’m good.” 

Kara grinned, nodding before she inched Bill’s shorts down, unearthing his substantial cock. Taking the condom, Kara rolled it over Bill and aligned herself above him. “You ready?”

Hands on her hips, Bill nodded and Kara gradually sank down, a fluttering gasp breaking from between her teeth as Bill’s thick cock stretched her open. “Oh Bill,  _ yes… _ ” She threw her head back, hips swirling to sense him against every inner surface as Bill placed a thumb over her clit.

As Kara hoisted her hips, Bill tried to be purposeful, intentional, to coax her swollen clit, to resist the urge to pick up the pace. But Kara rode him with a fury, arms draped over Bill’s broad shoulders, scarlet hair tumbling, mouth hanging open as her screams billowed, and before he realized it, Bill hooked his arm over her and began pounding Kara vigorously.

“ _ Oh Bill! Fuck! Your cock is so big! You feel so good! Yes! _ ” Kara cried, flickering around him as he hammered, Bill twisting his feet into the carpet and bracing his upper back into the couch.

“ _ Kara… _ ” Licking his lips, Bill summoned himself. “I love your pussy.  _ Fuck _ , you’re so warm.  _ Ride me! Yes!” _

Folding forward with a screech, Kara’s limbs fused around him as they rapidly pulsed. “ _ Bill! Bill, fuck! You’re gonna make me cum! You’re gonna make me cum so fucking hard!” _

“Yeah…” Voice soft, Bill fisted a hand in her auburn hair as he barreled into her. “Cum for me, Kara.  _ Cum for me.” _

Constricting violently, Kara stilled above him, hands splaying and mouth agape as her screams grew silent and she frantically dragged her pelvis back and forth over him in her final moments. Voice returning, her nails dug into his faded t-shirt with a gasp. “ _ Bill!” _

“ _ Kara!”  _ Scooting forward to the edge of his seat, Bill coiled his arms around her body, face nestled in Kara’s neck as he began yanking her down onto his throbbing cock while he slammed into her mercilessly. “ _ Fuck! Kara, yes! Fuck! _ ” Bill whimpered, months of pent up need boiling to the surface in tender noises that sounded like the desperate sounds of a begging man as his movements grew erratic. “ _ Fuck! Kara, I’m gonna cum! I’m gonna cum!” _ Eyes scrunched and clinging almost too tight, Bill swayed her to and fro, whining into Kara helplessly as his hips jerked forward before shivering, collapsing back onto the couch and gulping air.

Trembling against one another, Bill panted into the fabric of Kara’s dress rubbing circles into her back while her fingers danced in his hair until he went soft inside of her. Kara climbed off and Bill stood to throw away the condom before returning, Kara snuggling in beside him and placing a leg over his carved thighs. 

“Bill, um…” Adoringly caressing his belly, Kara rested her head on his mountainous shoulder. “Maybe this isn't a good time to ask, but...do I...do I still have a job?”

Bill pulled his head back, blinking. “Do you still want to work for me? I mean…” Glancing between them, he raised a prominent eyebrow. “If...if you want to keep doing this.”

“Yeah…” Kara nodded. “I mean, if that’s not too weird for you. You’re a good boss.” Tipping up, Kara kissed Bill’s rough cheek and smiled. “And you always treat me well. I think we could figure it out. At least until I find something else.”

Shrugging, Bill gathered Kara into the long line of his body. “Sounds good to me.”

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also take requests!


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